The Freight Show

Starting a brokerage from scratch is hard. Starting one at 55, after a 30-year career running brokerage at Schneider, OHL, Redwood, and ITS Logistics, is a different kind of bet — and doing it 18 months before the market collapses into a multi-year freight recession is something else entirely.

Greg Sanders has lived all of it. He grew up in the family business, an intermodal company his dad sold to Landstar in 1994. He spent 12 years at Schneider, helped build their brokerage division alongside Aaron Benzeland, and later sold the OHL brokerage to Brad Jacobs as XPO was just getting off the ground. After a run as CEO of ITS Logistics in Reno, Greg launched RDS Capacity Solutions in 2019 — partnered with the original RDS family (his dad's old attorney from the Landstar deal), brought in operators with skin in the game, and built a brokerage that returned all startup capital in six months and was profitable in year one.

Then COVID hit, the market ripped, and the 3.5-year slump arrived.

In this conversation, Greg breaks down what it actually takes to build a brokerage that survives a cycle like the one we just came through — the partner model, the pod structure, the recruiting playbook he learned from TQL, and why he believes the next three to five years will separate the brokers who integrate AI thoughtfully from the ones who don't. He also gets into his work with the TIA on broker liability, the F4A case in front of the Supreme Court, and what's broken about how FMCSA regulates carriers today.

What you'll learn:

• Why Greg started over at 55 and what made the RDS opportunity different from starting from zero
• The partner model behind RDS: skin in the game, equity ownership, and how Jeremy Inksroom grew his book 5x after joining
• Why the pod structure beats the traditional sales-and-carrier split on a big broker floor
• How field generals get paid on contribution margin, not top line — and why that changes everything
• What Greg learned from Brad Jacobs about M&A execution and why simplicity in the message wins on Wall Street
• The recruiting philosophy he stole from Kerry Byrne at TQL: send the executives to campus, not HR
• Why he hires athletes and looks for emotional intelligence over IQ
• How to integrate AI without alienating the operators who built the business
• The TIA's case on broker liability, the C.H. Robinson Supreme Court case, and what's at stake under F4A
• Why FMCSA has failed at carrier regulation and what's driving the chameleon carrier problem

Time-stamped highlights:

• (00:00) Intro: filming live at TIA Capital Ideas, hosted on borrowed Freight Caviar equipment
• (05:43) Greg's origin story: growing up in the family intermodal business, the two rules his dad set before he could join
• (07:24) Building the Southern California office for ITCO at 24 years old
• (08:28) Selling his dad's company to Landstar in 1994 and the Landstar agency model
• (11:46) Why Greg joined Schneider for "his MBA in trucking" and what he learned about asset operations
• (13:24) Don Schneider's playbook: deregulation, killing the unions early, doing it first class
• (17:43) The come-to-Jesus moment when Schneider asked him to move to Green Bay
• (19:02) Joining OHL, running North American transportation, and learning private equity from the inside
• (21:22) Selling the OHL brokerage to Brad Jacobs at the very start of XPO
• (23:24) What stood out about how Brad Jacobs transacts and integrates
• (25:47) Building the Redwood brand from a collection of acronyms (and why the URL was still available)
• (28:10) Managed trans vs. brokerage: the trade-offs and why brokerage executes better
• (32:02) Joining ITS Logistics in Reno, becoming CEO, and getting "sideways with a board member"
• (34:21) The dynamics of family office ownership and what changes when the board takes over
• (37:11) Starting RDS Capacity Solutions at 55 — the brand, the asset connection, and the partner setup
• (41:20) Why Mark Casey and Jeremy Inksroom — and how Jeremy grew his book 5x
• (42:19) Returning all startup capital in six months and being profitable in year one
• (43:19) Surviving the 3.5-year freight slump
• (44:09) Recruiting philosophy: what Greg learned from Kerry Byrne at TQL
• (46:05) Why he hires athletes and looks for emotional intelligence over IQ
• (48:59) The pod model: building $PnLs around field generals and paying on contribution margin
• (51:13) Why traditional sales-and-carrier splits break at scale
• (56:19) Becoming an expert in an industry, not an equipment type
• (59:48) Integrating AI without alienating the team — and why this is the next three-to-five-year challenge
• (01:05:49) Greg's involvement with the TIA and the three legs of advocacy, education, and networking
• (01:08:13) Broker liability, the C.H. Robinson Supreme Court case, and what F4A protection means
• (01:11:38) The chameleon carrier problem and how FMCSA has failed to regulate it
• (01:20:09) What gets Greg fired up: the movement of money, the movement of information, and what the next five years look like

Guest: Greg Sanders — President, RDS Capacity Solutions

Greg has spent his career building and leading brokerages, with executive roles at Schneider, OHL (acquired by XPO), Redwood Logistics, and ITS Logistics. He grew up in the family intermodal business his father sold to Landstar in 1994, and launched RDS Capacity Solutions in 2019 in partnership with the founding RDS family. He's been a member of the TIA since 1994 and serves on the board.

Most freight M&A deals look great on paper—but execution is where they succeed or fall apart. So what actually matters when you’re integrating teams, systems, culture, and operations while the market is turning against you? 

Jordan Strawn has lived every phase of that journey. He joined Reed Transport Services in 2015 when it was a $70M Tampa-based brokerage and helped scale it to $400M before Werner acquired the business in 2022. As COO through the growth years and now Senior Vice President of Logistics at Werner, Jordan has seen the full arc firsthand: scaling the company, navigating buyer interest, managing diligence, and leading integration on the other side of the deal. In this conversation, Jordan shares what made Reed an attractive acquisition target, how they built with discipline instead of chasing growth for growth’s sake, and what it really takes to make M&A work after the deal closes. 

He also breaks down the operational mindset behind successful integration, why process matters more than buzzwords, how Werner structured the business post-acquisition, and why power-only and refrigerated logistics are strategic parts of the company’s broader offering. 

What you’ll learn: 
- Why Reed became an attractive acquisition target: how service quality, repeatable execution, and strength in food & beverage and produce helped make the company stand out 
- What actually matters in M&A: how leadership teams think through diligence, cultural fit, employee continuity, and post-close execution 
- How to scale without losing focus: why Reed prioritized lane density, operational discipline, and core competencies over chasing every growth opportunity 
- What changes after an acquisition: the shift from operating a private business to leading inside a public company environment 
- Why process is a competitive advantage: how documented workflows, training, accountability, and tech-enabled visibility create operational consistency 
- How Werner approached integration: aligning teams, structures, and systems while keeping the business moving through a difficult freight market 
- The role of PowerLink and refrigerated power-only: how Werner’s trailer network creates capacity advantages and sticky carrier relationships 
- How multi-modal sales structure works: why centralized account ownership supported by mode specialists can improve the customer experience 

Time-stamped highlights:
- (00:00) Intro: Jordan’s triathlon training, upcoming Olympic race, and Ironman commitment 
- (03:53) The Reed origin story and how the company grew from its early days into a meaningful brokerage platform 
- (05:25) Jordan’s transition from UPS Freight into Reed and the move from operations into sales leadership - (06:16) Scaling Reed from $70M to $400M and the philosophy behind that growth 
- (06:58) The Werner acquisition and what made Reed strategically attractive 
- (08:22) Why Reed’s food & beverage and produce freight complemented Werner’s existing network 
- (09:43) Why process matters in both sales and operations 
- (13:04) What the acquisition process felt like while still running the business day to day 
- (14:48) Why there was strong buyer interest in Reed and how the team evaluated fit 
- (16:16) Building for quality, not just top-line growth 
- (18:45) Reed’s core competency in refrigerated truckload, food & beverage, and produce 
- (24:28) Jordan’s mindset during the sale and why team continuity mattered 
- (26:45) The challenge of preserving culture through M&A 
- (30:30) What actually changes after the deal closes: alignment, process, and decision-making 
- (32:33) How Werner structured sales and account management post-acquisition 
- (36:28) PowerLink explained and why power-only matters strategically 
- (42:08) Expanding into refrigerated power-only with connected reefer technology 
- (43:55) The building blocks of world-class operations 
- (48:15) How teams drive compliance through visibility, feedback, and execution discipline 
- (51:08) What keeps Jordan up at night: constant market change and keeping teams ready to adapt Guest Jordan Strawn — Senior Vice President of Logistics, Werner Enterprises Jordan spent nearly a decade helping scale Reed Transport Services from $70M to $400M before Werner acquired the company in 2022. 

He now leads Werner’s PowerLink and truckload brokerage operations, overseeing logistics teams across multiple offices and helping guide the ongoing integration of Reed into Werner’s broader logistics platform. Prior to Reed, he spent years in operations at UPS Freight, where he developed the process-driven mindset that continues to shape his leadership approach today. 

How does a 3PL evolve from a collection of entrepreneurial fiefdoms competing against each other to a unified, technology-enabled powerhouse? And what does it actually take to build exceptional operations in an industry where the basics—moving freight from A to B—haven't changed, but everything around it has?

Phil Shook has lived through every major transformation in modern freight. He started at Hub Group in 1994 when supply chain wasn't even a college major, joined CH Robinson in 1997 as the 40th employee in the Chicago South office (which ballooned to over 100 in just three years), and spent 23 years watching the company evolve through decentralization, the game-changing American Backhaulers acquisition, and the shift to unified operations. He led intermodal operations for years, managed railroad relationships worth hundreds of millions, and worked closely with the Backhaulers integration team—learning both the "Robinson way" and the scrappier, more tech-forward approach that would reshape the industry. After a stint in equipment leasing staying connected to carriers and railroads, he's now leading North America land transportation at Crowley, building a brokerage business from the ground up with truckload, LTL, intermodal, and dray—what he calls his "dream job" for the last chapter of his career.

This conversation is a masterclass in operational excellence and industry evolution. Phil breaks down the intermodal business model most people don't understand, explains why internal competition at pre-2000 CH Robinson sometimes mattered more than external rivals, reveals how the Backhaulers acquisition transformed Robinson's culture and technology, and shares what actually creates sustainable competitive advantage in brokerage (hint: it's relationships, but not the way you think). He also gets into why JB Hunt became the intermodal king, what the railroad business model teaches you about capacity planning, and why great operations teams are built on trust and alignment, not complexity.

**What you'll learn**

- **The intermodal business model decoded**: How rail + truck combinations work, why anything 700+ miles and within 100 miles of a rail hub can save double-digit percentages, and why JB Hunt's 150,000 container fleet makes them the undisputed leader—plus the nuances that don't show up on spreadsheets (like 80% of volume shipping Thursday-Friday changing your entire cost structure).

- **CH Robinson's cultural evolution**: How pre-2000 Robinson operated like franchises where offices competed against each other more than external rivals, why the 2000 American Backhaulers acquisition was "one of the most brilliant things the company ever did," and how Backhaulers' superior technology (the Express system) and individual-level entrepreneurialism reshaped Robinson into what it became.

- **Why relationships create operational advantage**: Not the surface-level "does your daughter play soccer" stuff, but how understanding shipper nuances (like discovering a lane's volume all hits Thursday-Friday), building direct relationships with receivers (so late trucks still get unloaded without accessorials), and knowing warehouse schedules lets you solve problems before customers even know they exist.

- **The railroad capacity planning challenge**: Why railroads historically struggled with unpredictable volume (not knowing if 100 or 400 containers would show up Chicago to LA), how they've shifted toward airline-style reservation systems to gain predictability, and why they're divesting container ownership to focus on their core competency of moving freight.

- **What makes exceptional operations orgs**: Phil's framework—it's not rocket science, it's about building great teams of detail-oriented, results-focused people passionate about being the best, then aligning them around common goals. The 90% that goes well is table stakes; differentiation happens in how you handle the 10% of exceptions through problem-solving, communication, and cost management.

- **Why 3PLs won the carve-out battle**: How the industry shifted from "we don't deal with brokers" to Fortune 100 companies deliberately allocating freight to 3PLs—because aggregating the 90%+ of carriers with fewer than 50 trucks into one relationship is more efficient than shippers chasing niche capacity themselves.

- **Technology's real role in brokerage**: Where tech genuinely adds value (in-transit visibility ending the "where's my truck?" game, automating unstructured data from emails/faxes into workflows, proactive exception alerts) versus where human relationships and judgment still dominate—and why customers still want to reach a human who understands the consequences of failure.

- **The intermodal identity crisis that wasn't**: How 20 years ago intermodal had PR problems, but now most freight that can go intermodal does—and if customers choose truckload pricing, it's a deliberate trade-off for cost certainty and recoverability (because when a train derails in Montana, there's zero recovery optionality).

**Time-stamped highlights**

- (00:00) From Enterprise Rent-A-Car interviews to Hub Group: Phil's accidental entry into logistics in 1994 when supply chain wasn't a college major

- (03:00) Joining CH Robinson in 1997 as the 40th employee in Chicago South—which grew to 100+ in three years

- (06:00) The decentralized Robinson model pre-2000: offices acting like franchises, GMs getting profit cuts, and internal competition mattering more than external

- (09:00) Creating five regional intermodal operating centers in 2000, then centralizing in 2005 to manage railroad relationships

- (12:00) The 2012 shift back to leading operations: getting hands dirty with customers and carriers again

- (15:00) Working on the American Backhaulers acquisition and learning "the true brokerage aspect, not just the Robinson way"

- (18:00) Intermodal 101: the rail + truck model, why 700+ mile lanes within 100 miles of rail hubs work, and double-digit savings potential

- (21:00) Why JB Hunt went all-in on intermodal: Mr. Hunt's visionary BNSF partnership 30+ years ago and how Hunt's now the largest with 150K containers

- (24:00) How intermodal works operationally: railroads own some containers (like TripLease), big players own their own fleets, chassis pools

- (27:00) The railroad capacity planning problem: not knowing if 100 or 400 containers arrive Chicago-LA, versus airlines' reservation model

- (30:00) Why railroads divested container ownership: focusing on core competency of moving freight, reducing cost complexity

- (33:00) What share of domestic freight goes intermodal and why more doesn't: customers know about it but choose truckload for cost certainty

- (36:00) The types of freight that work for intermodal: retail, F&B, transcontinental from Asia through West Coast, temp-controlled on expedited trains

- (39:00) Chicago and Memphis as railroad epicenters where all lines converge; why you might only have one railroad option depending on geography

- (42:00) The Backhaulers acquisition impact: their Express system "blew away" Robinson's tech, ultra-entrepreneurial culture at individual rep level

- (45:00) The 2010s evolution toward "one team" Robinson: realizing external competition required focusing efforts outward, not fighting internally

- (48:00) What creates sustainable success at CH Robinson: Dave Bozeman's turnaround from Wall Street skepticism to "darlings" with 30-40x multiples

- (51:00) Building exceptional operations orgs: g...

Most freight brokerages are drowning in AI pilots that never make it to production. The gap between a working demo and a system processing thousands of loads per week is not technical — it is organizational.

It comes down to setting clear KPIs up front, running biweekly AI steering committees with full leadership visibility, and being ruthlessly honest about what is working and what is not.

Jonathan Drouin has lived both sides of this equation. He started as a software developer at 19, moved his first freight load in 2012 at Bear Transportation under Michael Kaney, built and sold his own TMS company and brokerage, then joined WWEX (formerly Worldwide Express) in 2019 to lead truckload technology.

Over seven years, he has helped scale the company from $2B to $5B through the GlobalTranz merger and 35+ acquisitions — migrating systems, integrating business units, and now spearheading AI deployment across the entire quote-to-cash workflow.

Today, he oversees product strategy and AI initiatives for a company where freight mix is roughly 40% LTL, with the rest split between parcel and truckload, serving primarily SMB and mid-market shippers as the largest UPS reseller in North America.

In this conversation, Jonathan breaks down the exact framework WWEX uses to deploy AI: how they mapped every workflow from quoting to cash, prioritized initiatives against three hard metrics — customer retention, margin growth, and cost reduction — launched a dozen AI projects in year one to stress-test the boundaries, and now run every initiative through a rigorous steering committee with predefined KPIs and public accountability.

He explains why email AI and repetitive tasks deliver the fastest ROI, why they shifted from build-first to partner-first as model complexity increased, the change-management discipline that separates successful deployments from expensive experiments, and why he believes AI will chip away at exception handling far beyond today’s repetitive-task automation.

What you’ll learn

• The three-pillar AI prioritization framework: How WWEX evaluates every AI initiative against customer retention, margin growth, and cost reduction — and why vague goals like “quality of life improvements” do not make the cut in a private-equity-backed, results-driven culture.
• Why email AI wins first: The specific reasons email-based automation like quoting and carrier communication delivers faster ROI than other channels — customers do not know AI is involved, responses are faster, and workflows are linear enough for today’s models to handle exception management effectively.
• From 60 ideas to 12 deployments: The exact process WWEX used to map workflows role by role and team by team, stress-test assumptions with business leaders educated on AI capabilities, and narrow down to initiatives with clear, measurable outcomes tied to business KPIs.
• Build vs. partner: the 2025 inflection point: Why Jonathan went from bullish on internal builds to heavily favoring vendor partnerships — hyper-funded vendors with MIT and Carnegie Mellon talent can deploy 5–7 engineers on your use case, technology is moving too fast to bring costs in-house, and partnering enables more experimentation at lower risk.
• The AI steering committee model: How running biweekly reviews with top leadership and all business stakeholders — where every project’s KPIs are public and visible from day one — creates accountability, forces intellectual honesty, and separates projects that deliver from expensive learning experiences.
• Prototype to production: the 5% to 50% problem: Why getting a functional AI demo working on 1% of use cases takes almost no time, but scaling to 50% production reliability is a months-long journey — and why most people underestimate this gap until they have shipped something real.
• Repetitive tasks today, exception handling tomorrow: Jonathan’s contrarian view that AI will move upstream faster than people think — today it handles repetitive work, but as models gain more context from email history, phone transcripts, and CRM data, they will chip away at exceptions that require a person today, like invoice mismatches or missing PO numbers.
• Change management as the real bottleneck: Why the biggest barrier to AI ROI is not the technology — it is cultural buy-in, setting clear outcomes up front, and having the organizational discipline to push through resistance when the destination is clear and the product works.
• Why PepsiCo and other shippers built internal brokerages: The logic behind turning transportation spend into a profit center, why these initiatives often plateau after aggressive early growth, and how market downturns expose the same cash-flow and margin challenges traditional brokers face.
• The non-optional AI moment for every company: Why Jonathan believes companies resisting AI adoption risk becoming the next Kodak, why “quality of life” improvements do not cut it anymore, and how WWEX’s M&A-hardened culture of rallying around big decisions enables faster, more disciplined change management than most peers.

Time-stamped highlights

• (00:00) From French-Canadian immigrant to software developer at 19: How Jonathan’s dad put IT books in his hands and sent him to a customer site, leading to a non-linear path from clinical software to freight brokerage at Bear Transportation under Michael Kaney in 2012.
• (03:30) Early career arc: CH Robinson via Phoenix acquisition, PepsiCo’s internal brokerage, then raising venture capital to build his own TMS company and freight brokerage in 2016–2017 — using his own software to prove the efficiency thesis.
• (06:45) Why PepsiCo started a freight brokerage: The executive-level logic of turning billions in transportation spend from cost center to profit center, leveraging massive private fleets and backhaul opportunities, and the typical growth-then-plateau trajectory of shipper-owned brokerages.
• (09:30) The shipper-brokerage plateau pattern: Why these initiatives often stall after hitting a certain scale — the same market disadvantages as traditional brokers, cash-flow challenges when you are in the business of making product, and waning executive excitement as the model matures.
• (12:00) Building vs. buying a TMS: Jonathan’s journey from building his own TMS to now making billion-dollar TMS decisions at WWEX — why stability and people/process alignment matter more than cutting-edge tech, and when building makes sense.
• (15:30) WWEX structure and strategy: How the $5B company operates across three go-to-market brands — Worldwide Express, GlobalTranz, and Unishippers — splits roughly 40% LTL and 60% parcel/truckload, and serves SMB and mid-market as the largest UPS reseller in North America.
• (18:00) Multi-mode sales structure: Why WWEX splits LTL/parcel reps from truckload reps — sales behavior naturally gravitates toward what reps are successful at, so specialization by mode drives better outcomes than training one rep on everything.
• (20:45) Jonathan’s evolving role at WWEX: From truckload platform buildout in 2019, through GlobalTranz integration and multiple migrations, to revenue operations and AP work with LTL carriers, then shifting to AI strategy in 2024 and now overseeing product strategy with heavy focus on the agent channel.
• (24:00) Mapping the AI opportunity: How WWEX went role by role, team by team, workflow by workflow to map the entire q...

Freight doesn’t slow down at the dock. It slows down in the yard, at the gate, and in the messy handoff between facility ops and transportation. Chris has spent decades inside that “supply chain execution” layer, and he’s now building a modern yard operating system at Terminal Industries to remove the friction most networks have learned to tolerate.

In this episode, Chris Brumett, Chief Product Officer at Terminal Industries, breaks down how warehouses actually optimize (labor travel time, staging space, dock throughput), why carrier appointment compliance is a facility survival mechanism, and how low-visibility yard operations quietly create expensive downstream inefficiency. We also dig into the technology shift powering the category, from ASNs and appointment scheduling to computer vision and AI-driven workflows that reduce gate congestion, improve trailer/chassis visibility, and tighten execution across the full facility visit.

What you’ll learn

• Dock-Driven Warehouse Optimization: How product velocity, storage zones (ambient vs. temp-controlled), and travel time dictate door assignments and labor planning.
• ASN Visibility and Receiving Automation: Why ASNs matter, how they connect to scanning and inventory accuracy, and where “ideal state” still breaks down.
• Tendered vs. Operating Carrier Validation: How load brokering creates identity ambiguity at the gate and why facilities need separation between tendered carrier, operating carrier, and cargo asset.
• Appointment Windows as Labor Control: The real reason strict appointment rules exist, how staging creates dock congestion, and why facilities penalize missed windows.
• Inbound Priority Logic From Outbound Demand: How facilities prioritize inbound based on outbound shortages, retail promotions, and SKU velocity, not “fairness” to carriers.
• Drop Trailer Strategy and Yard Buffering: Why drop-and-hook creates slack that smooths operational variance, and when yard footprint becomes the constraint.
• The Hidden ROI of Yard Execution: Why optimizing “five spotters” misses the point, and how yard inefficiency causes dock labor idle time and throughput loss.
• From Point Tools to Yard Operating System: How Terminal approaches the yard as an end-to-end workflow problem, not a check-in camera or a spreadsheet replacement.
• Computer Vision and AI Workflow Automation: Where CV reduces gate processing time, and how AI can automate repetitive operational steps without removing the human-in-the-loop.
• Facility ROI Levers That Actually Pencil: Labor displacement/reallocation, detention and demurrage reduction, and scaling volume without scaling labor.

Time-stamped highlights

• (01:40) Warehouse Operations and What Facilities Optimize For
• (04:44) How Warehouses Actually Optimize Labor and Inventory
• (08:05) Warehouse Management Systems and Labor Efficiency
• (10:17) Advanced Shipping Notices, EDI, and Inbound Visibility
• (12:21) Carrier Visibility Gaps and Multi-Broker Complexity
• (15:08) Appointment Scheduling and Labor Planning Mechanics
• (17:28) Why Appointment Compliance Drives Facility Efficiency
• (22:11) Staging Loads and Dock Congestion Tradeoffs
• (23:32) Freight Prioritization Based on Product Urgency
• (27:00) Retail Promotions and Inbound Acceleration
• (29:49) Facility Optimization vs. Shipper-of-Choice Tradeoffs
• (35:17) The Yard as the Forgotten Operational Lever
• (40:28) Spotter Inefficiencies and “Asteroid Hunt” Yard Problems
• (44:42) Terminal’s Yard Operating System Approach
• (51:11) Customer ROI, Labor Savings, and Throughput Gains

Guest

Chris Brumett — Chief Product Officer, Terminal Industries
Chris Brumett is the Chief Product Officer at Terminal Industries and a longtime supply chain execution operator focused on warehouse and yard technology. He has spent roughly 30 years building software that improves operational execution, with the last 15 years centered on yard management and the systems that connect facilities, assets, and transportation providers.
LinkedIn: https://www.linkedin.com/in/chris-brumett-6a04201/

Links & references

• Terminal Industries (Company): https://terminal-industries.com
• Chris Brumett Profile (Terminal / org directory): https://theorg.com/org/terminal-industries/org-chart/chris-brumett
• ANSI X12 856 (Advance Ship Notice / Ship Notice): https://www.stedi.com/edi/x12/transaction-set/856
• GS1 Overview of ASN (Advance Ship Notice) Standards: https://www.gs1.org/standards/edi
• Council of Supply Chain Management Professionals (CSCMP) — Supply Chain Resources: https://cscmp.org

Brought to you by

VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

The freight market looks very different depending on which side of the phone you sit on. Will Kerr has lived both sides deeply, first as a carrier sales operator and brokerage founder who scaled Edge Logistics to $10M in its first year and over $160M in revenue, then as a trucking executive navigating today’s broker-driven freight environment. His perspective cuts through a lot of surface-level advice by unpacking the mechanics that actually determine who gets freight covered, who absorbs risk, and where margin is really made.

In this episode, William Kerr, President at Price Rite Transport and Founder and former CEO of Edge Logistics, breaks down how Edge scaled by building carrier density instead of chasing volume, what separates high-performing carrier reps from the rest, and how internal brokerage dynamics quietly decide which loads get covered and which go negative. We also dig into capacity realization risk, why “autobook” freight is the real profit center inside large brokerages, how carrier tagging and internal trust are earned, and why a disciplined, broker-centric carrier strategy can outperform direct shipper relationships in the current pricing, compliance, and payment environment.

What you’ll learn

• Carrier Density as a Productivity Engine: Why top carrier reps drive volume through a small bench of relationship carriers to reduce rate thrash and increase repeatability.
• The 50–500 Truck Sweet Spot: How mid-size fleets unlock lane-level consistency, and why those carriers are the hardest to win and retain.
• Carrier Ownership and Tagging Mechanics: How “exclusive use” works inside big brokerages, including minimum booking thresholds and time-based earning rules.
• Internal Deal Selling in Split Models: Why carrier reps sell deals internally to customer reps and managers, and how that determines who gets the freight.
• Minimum Fees and Loss Allocation: How carrier-side minimums are structured and why losses typically roll to the customer side when markets turn.
• Capacity Realization as a Hidden Risk Lever: How booking two weeks out can turn into same-day chaos when carriers shop loads and fall off late.
• Why Loads Go Negative Fast: How day-of repricing at 30–100% higher rates can flip a marginal load into a multi-hundred-dollar loss.
• Autobook Freight and Tribal Knowledge: How the best reps pre-position capacity and become the default option when “easy money” freight hits the board.
• Carrier Compliance in the Digital Era: Why digital footprint scoring and broker-centric reporting systems can block legitimate carriers from freight flow.
• Carrier Consolidation as a Reset Button: The operational steps behind merging six carriers into one brand—dispatch, safety, systems, fleet branding, and go-to-market.

Time-stamped highlights

• (01:20) From CME Trading Floors to Truckload Freight
• (03:10) Learning Carrier Sales Inside Echo Logistics
• (05:30) Commission Changes and Talent Flight
• (07:30) Launching Edge From a Trailer
• (09:30) Scaling a Carrier-First Brokerage Model
• (12:00) What Made Great Carrier Reps Win
• (14:10) The 50–500 Truck Carrier Sweet Spot
• (17:10) How Carriers Get Locked and Tagged
• (19:10) Losses, Minimum Fees, and Split Models
• (22:00) The Myth of “No Trucks”
• (24:30) Becoming a Broker of Choice for Carriers
• (27:20) Tribal Knowledge and Auto-Book Freight
• (30:10) Capacity Realization Failures
• (35:10) Carrier Compliance in a Digital Vetting Era
• (41:30) Consolidating Fleets Into One Brand

Guest

William Kerr — President, Price Rite Transport
William Kerr is President of Price Rite Transport and Founder and former CEO of Edge Logistics, where he built a carrier-first brokerage that scaled to enterprise volume. He brings a rare operator’s view of both brokerage carrier sales and trucking network strategy.
LinkedIn: https://www.linkedin.com/in/william-kerr-92275363/

Links & references

• Price Rite Transport: https://www.priceritetransport.com/
• Edge Logistics: https://www.edgelogistics.com/
• Echo Global Logistics: https://www.echo.com/
• Traffic Tech: https://www.traffictech.com/
• Highway: https://www.highway.com/

Brought to you by

VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

Freight companies that scale well usually share one thing in common: they obsess over the operating details that keep the business from breaking as headcount, customers, and complexity explode. Reliance Partners President Chad Eichelberger has built his career inside that reality, from early-stage brokerage growth to enterprise-scale execution and risk management.

In this episode, Chad walks through two rare zero-to-scale runs—helping grow Access America from an early-stage Chattanooga startup into a brokerage that reached a $675M run rate before selling to Coyote, then applying the same scalability discipline to build Reliance Partners into a specialist insurance platform for trucking and logistics. We unpack the metrics and cultural rules that made the brokerage model work at scale, plus the new risk reality for brokers today—where strategic cargo theft and fraud are reshaping underwriting, controls, and the true cost to serve.

What you’ll learn

• How to design brokerage growth that scales (not just grows): The input metrics Access America measured (talk time, calls, pipeline hygiene) and why “small” behaviors become massive leading indicators.
• How to build a competitive sales culture without breaking teamwork: The CRM rules, account ownership enforcement, and RFP adjudication process that kept teams aggressive and aligned.
• Why cradle-to-grave worked—and where hybrid structures emerged: How large enterprise accounts naturally evolved into regionalized “enterprise pods” while keeping accountability tight.
• What elite cold calling really looked like: Gatekeeper navigation, dial-by-name tactics, and the persistence that turns “years of voicemails” into a top customer.
• What a “never say no” service mindset costs—and why it pays: The $32K charter-plane shipment loss that reinforced execution as a brand advantage.
• How insurance scales differently than brokerage sales: Why insurance is often “win it all or win nothing,” and how renewals create an annuity-like book when service stays tight.
• How broker risk has shifted from catastrophic liability to high-frequency cargo losses: Why strategic theft and fraud are forcing new controls—and raising the cost of coverage.
• What underwriters actually evaluate: Vetting stack, loss history, commodities, contracts, compliance maturity, and why the pool of active underwriters is tighter than most brokers assume.
• How to reduce theft exposure: Repeat-carrier discipline, high-value protocols, anomaly detection signals, and why “one exception” often becomes the breach.
• Why 2026 feels different: The optimism case for a healthier market—if the macro picture doesn’t break.

Time-stamped highlights

• (01:05) Early Access America Origins
• (02:40) Entering Brokerage as a Young Seller
• (03:33) Rising Through the Ranks
• (05:25) What Actually Scales a Brokerage
• (06:19) Metrics, Measurement, and Process Discipline
• (08:24) Competitive Culture at Access America
• (10:12) Sales Training and Battle-Tested Reps
• (11:16) Cold Calling That Works
• (16:01) Competition Without Breaking Teamwork
• (18:08) CRM Discipline and Account Ownership
• (20:05) Cradle-to-Grave vs. Chicago Model
• (25:29) Transitioning Through the Coyote Merger
• (27:05) Building Reliance Partners
• (32:00) Why Transportation Insurance Is Fragmented
• (42:35) Rising Risk and Changing Insurance Requirements

Guest

Chad Eichelberger — President, Reliance Partners
Chad Eichelberger is President of Reliance Partners, the largest standalone insurance agency dedicated exclusively to the transportation and logistics industry, insuring more trucking fleets in the U.S. than any other agency. Previously, he served as President of Access America Transport through its merger with Coyote Logistics, bringing deep experience in scaling freight brokerages, building high-performance sales organizations, and managing risk at enterprise scale.

LinkedIn: https://www.linkedin.com/in/chadeichelberger/

Links & references

• Reliance Partners: https://reliancepartners.com/
• Access America Transport + Coyote deal coverage (growth + transaction context): https://www.chattanoogan.com/2014/11/17/288154/Coyote-Logistics-Merging-With.aspx
• UPS acquisition of Coyote Logistics: https://www.ups.com/assets/resources/media/en_US/20150812_UPS_Coyote_Deal_Deck.pdf
• C.H. Robinson Worldwide, Inc. v. Miller (No. 20-1425): https://www.supremecourt.gov/docket/docketfiles/html/public/20-1425.html

Brought to you by

VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

If you sell into enterprise shippers, here’s the uncomfortable truth: your differentiator isn’t your pitch deck, your coverage story, or even your rate. It’s whether you can deliver predictable service and predictable economics inside a network built to eliminate volatility.

This episode pulls back the curtain on how a large enterprise shipper actually runs transportation procurement. Paul Estrada has spent nearly two decades leading procurement at scale, and he breaks down what most providers miss: the internal “cost vs. service” tug-of-war, why procurement lives on a scoreboard, how routing guides stay intact when markets swing, and what it really means to be a low-cost-to-serve partner. We get into radical data transparency, carrier enablement, index-based pricing, and why the best providers don’t just quote lanes—they explain the math behind sustainable pricing.

What you’ll learn

• How enterprise supply chains are actually organized: Why procurement, operations, manufacturing, and customer teams optimize for different goals—and how those tensions are managed.
• The two metrics that matter more than all others: Getting product where it’s needed, when it’s needed, at the lowest sustainable cost.
• Why procurement lives on a scoreboard: How performance is measured in dollars and cents—and why market cycles can make teams look like heroes or villains overnight.
• How enterprise shippers manage cost volatility: Dedicated capacity, portfolio mix, and risk mitigation as insurance—not ideology.
• Why carrier-agnostic procurement wins: How decisions are made across brokers, asset carriers, and dedicated fleets based on utilization and economics—not labels.
• What shippers actually look for in brokers: Sustainable pricing, operational intelligence, and the ability to explain how rates work—not just what they are.
• Why deep data sharing creates better pricing: How transparency around volumes, seasonality, and operating constraints leads to routing guides that hold up.
• How carriers are onboarded like employees: SOPs, portals, escalation paths, and training as a way to reduce churn and execution risk.
• The “Goldilocks” provider strategy: Why fewer, deeper relationships outperform wide, fragmented networks over time.
• How AI matters to shippers (and how it doesn’t): Why buzzwords don’t win business—but lower transaction costs do.

Time-stamped highlights

• (00:00) Paul Estrada and the Enterprise Shipper Lens
• (01:12) Breaking into Supply Chain and Procurement
• (02:42) Inside a Large Enterprise Logistics Organization
• (05:19) The Two KPIs That Everything Rolls Up To
• (06:40) Cost vs. Service and Internal Tension
• (08:52) The Operations Team as the Balancing Layer
• (10:16) Promotions, Firings, and the Procurement Scoreboard
• (12:27) Managing Risk and Volatility Across Cycles
• (14:46) Service Performance and Failure Points
• (16:31) Data Infrastructure and Fast Decision-Making
• (18:19) Optimization as a Cultural Advantage
• (20:45) Portfolio Thinking Across Carriers and Brokers
• (22:51) Brokers in Contractual Freight
• (24:18) Evaluating Provider Sustainability and Risk
• (25:54) Radical Data Sharing and Pricing Stability
• (30:08) Building a High-Quality Carrier Bench
• (33:47) What Separates Long-Term A-Player Providers
• (37:04) Becoming a True Shipper of Choice
• (40:21) Reading the Market and Rate Cycles
• (43:48) Index-Based Pricing and Trust-Based Partnerships

Guest

Paul Estrada — Director of Procurement, Niagara Bottling
Paul Estrada has spent nearly 20 years in transportation and supply chain leadership, with deep experience across operations and procurement at enterprise scale. He leads procurement strategy focused on cost optimization, service reliability, risk management, and long-term carrier partnerships—bringing a data-driven, relationship-oriented approach to one of the most complex logistics networks in the industry.

LinkedIn: https://www.linkedin.com/in/paulmestrada/

Links & references

• Niagara Bottling: One of the largest beverage manufacturers in the U.S. with a highly optimized supply chain — https://www.niagarawater.com/
• Dedicated vs. One-Way vs. Brokered Freight Models: Portfolio approaches to capacity and risk management
• Index-Based Freight Pricing: Contract structures tied to market indices

Brought to you by

Vooma - Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

The freight market has trained most brokerages to chase volume, compete on price, and treat service lines like shiny add-ons. Evans Transportation took the opposite approach: build a durable business by leaning into complexity, building culture as a competitive advantage, and diversifying with discipline.

In this episode, Ryan Keepman shares how Evans — one of the rare family-owned brokerages still standing from the deregulation era — evolved from a Wisconsin brokerage built on relationships into a multi-division logistics operator supporting everything from envelopes to excavators. We unpack the real mechanics behind service-line expansion, why the “jack of all trades” strategy kills trust, and how Evans uses intentional culture and in-person connection to keep remote teams aligned as the company scales.

What you’ll learn

• How Evans Transportation survived deregulation and stayed family-owned: Why relationship-driven brokerage and early operational investments helped Evans outlast consolidation.
• The real reason Evans diversified into multiple divisions: Diversification wasn’t a growth gimmick—it was a strategic defense after losing top clients and recognizing weaknesses in truckload execution.
• Truckload procurement vs. traditional brokerage: How Evans built a carrier procurement engine designed to protect managed transportation performance rather than operate as a pure sales brokerage.
• The modern 3PL approach and blind bidding: How Evans structures managed transportation so shippers can keep multiple brokers in the mix while Evans competes fairly without undercutting.
• How managed transportation adoption has changed: Why most shippers are already using 3PLs, how the sales cycle has shifted to CFOs and VPs, and why strategic sponsorship matters.
• Why Evans avoids price wars and “broker poker freight”: Their focus on value, complexity, and long-term trust instead of transactional spot quoting.
• How to build trust by saying no: Why Evans intentionally accepted only 3 of 13 specialized moves to avoid failure and earn long-term credibility.
• The blueprint for launching new service lines: Why face-to-face time, slowing down, and releveling teams matters more than speed when integrating new divisions.
• Evans’ culture operating system: Quarterly in-person rhythms, shared experiences, and a “do life together” philosophy that fuels cohesion across remote leadership.
• AI as a relationship accelerator: How automation reduces noise so brokers can invest in carriers, deepen relationships, and drive better outcomes.

Time-stamped highlights

• (00:00) Introduction to Ryan Keepman and Evans Transportation
• (01:14) The Early Years and Founding Story
• (03:48) Starting Evans with High Risk and Early Challenges
• (07:32) Evolution from Brokerage to Managed Transportation
• (08:16) Early TMS Development and Technology Advantage
• (09:19) Leadership Transition to Ryan
• (10:02) Diversification Strategy and the Truckload Division
• (11:07) Expansion into Mexico, Specialized, Parcel, and Government
• (13:09) Managed Transportation and Truckload Procurement
• (16:28) Modern 3PL Model and Blind Bidding
• (19:55) Shipper Trends and Managed Transportation Adoption
• (24:35) Building a Moat with Parcel and Full-Suite Solutions
• (25:46) New Warehouse Product and Strategic Fit
• (28:28) Avoiding Price Wars and Competing on Complexity
• (32:00) Building Trust Through Gradual Growth and Saying No
• (35:08) Lessons Learned in Launching New Service Lines
• (40:08) Evans Culture and the “Do Life Together” Approach
• (44:16) Leading Distributed Teams with Quarterly In-Person Rhythms
• (48:10) Leadership Growth, Directness, and Personal Reflection

Guest

Ryan Keepman — CEO, Evans Transportation
Ryan Keepman has spent 19+ years at Evans Transportation Services, building his career across key accounts, sales leadership, and executive leadership roles. He became CEO in December 2020 after serving as President (2018–2020) and previously leading growth as Vice President of Logistics Sales (2014–2020) and Vice President of Key Accounts (2007–2020). Under his leadership, Evans has evolved into a diversified logistics partner spanning managed transportation, truckload procurement, Mexico, specialized solutions, parcel, government services, and new warehousing offerings—while maintaining a people-first culture built on trust, accountability, and shared experience.
LinkedIn: https://www.linkedin.com/in/ryan-keepman-75246610/

Links & references

• Evans Transportation: Family-owned logistics provider offering managed transportation and multimodal solutions — https://www.evanstrans.com/
• Strength to Strength (Arthur C. Brooks): A framework for reinvention and sustaining fulfillment through midlife transitions
• Transportation Deregulation (Motor Carrier Act of 1980): The policy shift that reshaped the freight brokerage industry

Brought to you by

VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

The real bottleneck in freight technology isn’t innovation — it’s adoption, misaligned incentives, and the absence of ownership over cultural change. Jeff Dangelo has lived every side of that problem: early at TQL, helping scale MegaCorp Logistics, founding the freight collaboration platform Turvo, and now leading Fura as CEO.

In this episode, Jeff breaks down what really makes brokerages scale (and where common models break), why most “digital transformation” initiatives stall, and how Fura’s acquisition strategy targets underperforming brokerages and gets them from manual to digital in a matter of months. We dig into the trust-building required to integrate teams, how to decide whether to build vs buy software, and why AI can shrink the adoption gap by running “in parallel” with people — not forcing everyone to change overnight.

What you’ll learn

• How freight brokerages actually scale: Why TQL “played the percentages,” built a culture engine, and used hiring + activity math to compound growth.
• Cradle-to-grave vs team-based brokerage models: What breaks in the classic spin-out approach, and how MegaCorp kept teams intact to protect continuity and service.
• Why most digital transformations fail: The real blocker isn’t software — it’s behavior change, incentives, and lack of discovery/business-case selling.
• Fura’s M&A thesis in a down cycle: The three seller buckets, why “losing money or break-even” firms can be ideal, and how Fura modernizes fast.
• How to integrate culture without breaking it: The “earn trust” approach — engagement loops, surveys, all-hands, and executive sponsorship.
• Build vs buy decision-making: The matrix Fura uses (speed, business case, differentiation/IP) to decide what to own vs partner for.
• Network-based selling in freight: How Fura maps nodes (vendors/customers/suppliers), uses proof of impact, and links sales + ops to drive adoption.
• AI as an adoption accelerator: Why AI can run in parallel with people to reduce friction — and how that reshapes brokerage into a more strategic model.

Time-stamped highlights

• (00:00) Tech Adoption and the Manual-to-Digital Gap
• (01:00) Jeff Dangelo’s Freight and Tech Background
• (04:00) Early TQL and Boiler Room Culture
• (07:00) TQL’s Hiring and Scaling Engine
• (10:00) Data-Driven Growth and Hurricane Interns
• (14:00) The Cradle-to-Grave Churn Problem
• (18:00) MegaCorp’s Team-Based Fix
• (23:00) Selling Freight vs Selling Software
• (28:00) Turvo and the Adoption Challenge
• (33:00) Fura’s Consolidation Strategy
• (37:00) The Three Seller Buckets
• (41:00) Structuring Turnaround Deals
• (45:00) The Integration Trust Playbook
• (48:30) Standardizing Systems at Scale
• (50:30) Build vs Buy Decisions
• (51:30) The Future of Brokerage With AI
• (52:04) Closing Thoughts on Execution Over Vision

Guest
Jeff Dangelo — Co-Founder and CEO, Fura
Jeff is a freight industry veteran with 20+ years across brokerage, technology, and M&A. He helped scale TQL and MegaCorp Logistics, founded Turvo, and now leads Fura, where the team acquires and modernizes brokerages by combining automation, execution, and disciplined integration.
LinkedIn: https://www.linkedin.com/in/jeff-dangelo-8a7107a/

Links & references

• Fura: Brokerage + modernization platform focused on acquiring and digitizing underperforming brokerages — https://fura.com/
• Turvo: Freight collaboration platform Jeff founded focused on shared workflows across shippers, brokers, and carriers — https://turvo.com/
• TQL: High-output brokerage known for systems-driven hiring, training, and culture — https://www.tql.com/
• MegaCorp Logistics: Brokerage scaled with a more team-based operating model and continuity focus — https://www.megacorplogistics.com/

Brought to you by

VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/